Azo dyestuffs insoluble in water and fiber dyed therewith



Patented June 27, 1933 UNITED STATES PATENT FFICE ARTHUR ZIT SGHER, OFOFFENBAGH-ON-THE-MAIN, GERMANY, ASSIGNOR TO GENERAL ANILINE WORKS, INC.,OF NEW YORK, N. Y., A CORPORATION OF DELAWARE AZO D'YESTUFFS INSOLUBLEIN WATER AND FIBER DYED THEREWITI-I.

No Drawing. Application filed August 26, 1931, Serial No. 559,597, andGermany August 29, 1930.

My present invention relates to new azo therewith.

These dyestuffs correspond to the general formula: I

wherein R means a radical of the benzene,

naphthalene, anthracene, acenaphthene, car-' bazole or quinoline serieswhich radical may contain halogen, nitro-,-alkoxy-, alkyl-,dialkylamino-sulfonyl: ['(alkyl) N-SO alkylsulfonylorphenylamino-carbonyl- (C ILNHCO) groups and wherein n means the number 1or 2. They are obtained by combining the diazo compound ofl-amino-{t-methyl 2.5- di n butyloXy-benZene-with a(Q-hydroxy-naphthalene-3-carbonyl) amino-aryl, wherein aryl means theradical signified in the above formula by R. I I

They may be produced in substance and used for making color lakes orthey may be prepared on fibers. As fibers suitable for the production ofthese dyestuffs thereon may be named: animal fibers (for example, silk)native cellulose (for example, cotton), regenerated cellulose (forexample, viscose).

The dyeings thus obtained show reddish violet to blue shades and aredistinguished by a good fastness, especially to peroxidebleaching. Thelatter operation consists in treating at a temperature rising from 40 C.to about 80 C. for hour 1 part of dyed material with 10 parts of asolution containing per liter 2 grs. of sodium peroxide and 6 grs. ofwater-glass.

By the present invention the possibility of producing violet and bluedyeings by means of the ice color 'method is enlarged since among thediazo compounds of the benzene series'only those containing a furthernitrogeneous group were hitherto know to turn dyeing.

the shade sufficiently to the blue end of the spectrum.

In order to further illustrate my invention, the following examples aregiven. I wish it, however, to be understood that I am not limited totheparticular products or reaction conditions mentioned therein.

Example 1 mg a reddish violet dyeing of a very good fastness to chlorineand to peroxide is obtalned. The dyestuff thus produced on the fibercorresponds to the formula:

OI C4119 04110 O OHE 1- (2 hydroxy-naphthalene-3- carbonyl)amino-3-methoxy-benzene yields with the same diazo compound a darkbluish violet Example? Cotton yarn previously treated in' an appropriatemanner'is impregnated with a solution containing per liter 4 grs. of1-(2-hydroxy naphthalene 3 --carbonyl) amino--3- chloro-benzene, 8 cc.of caustic soda solution of 3l Be. and 10 cc. of Turkey red oil. Thenthegoods are well dehydrated and developed as described in Example 1.Inthis manner a blue dyeing of a very good fastness to chlorine and toperoxide is obtained.'- The dyestufi thus produced on the fibercorresponds to the formula:

(Z-hydmxy-Q ph ha m 3 -car ny. amino-2-chloro-benzene yields with thesame diazo compound a reddish violet dyeing Example 3 example,sulfite-cellulose 1 waste liquor, .the

temperature being maintained at about 25 C. After 15 minutes, 10 grs. ofcommon salt are added and the goods are again handled for 'ofan' hourand well dehydrated. Thereafterthey are developed in a bath which cntains per liter the diazo compound of 2.6 grs. ofl-amino+4-methyl-2.5-di-nbutyl-oxy-benzene, 5 cc. of an acetic acid ofstrength and 10 grs. of common salt, the mineral acidhaving beenneutralized with sodium acetate. After soaping, rinsing and drying areddish violet dyeing is obtained. The dyestuif thus produced on thefiber'corresponds to the formula: i i

'1 2 hydroxy naphthalene 3 carbonyl amino-2-methyl-l-chloro-benzene, 3cc. of caustic soda solutionof 34 B6. and '10 cc. of Turkey red oil.Then the goods are well centrifuged and developed in a solution whichcontains the'diaZo compound. if-2.6

I grs. jof l-amino-a-methyl-fl.5-di-n-butyl-oXy= benzene per liter, theexcess of mineral acid having beenneutralizcd with sodium acetate.After-rinsing and soaping a dark blue dye: ing, s obtained. The-.dye,stufi thus. pro:

alkylsulfonylduced on the fiber corresponds to the for mula:

H OH:

A similar, somewhat more reddish dyeing is produced by means of 1-(Q-hydroxy-naph- 'thaIene-3-carbonyl) -amino-2-methyl-benzene and thesame diazo compound.

The dyestufis may also be produced according to one of the customaryprinting processes.

The following table shows the shadesof some other. dyestuffs of thiskind the diazo compound of 1-amino-4-methyl-2.5-dienbutyl-oxy-benzeneyields with the (Q-hydroxynaphthalene-3-carbonyl) compound of Shadeamino-benzenm... Reddlshvlolet. l-aminogfimitro-benzeneu Do.Lamina-naphthalene. Do, 2-amino-naphthalene Dark violet. l-amlnoi2-ethory-benzene, Reddlshvlolet. 1-ami no4-methy1-benzene. Do.1-am1no-2-methoxy-benzene.- Do. 1-amino-.4-ch1oro-.benzene Do.1-amlno-3.4-dichloro-benzene 'iolet. 1-amino-2 methoxyv5-chloro-ben;ene,Reddish violet. l-amino-2-methoxy-4-chloro-benmne- Do.l-amino-Zfi-dimethoxy-benzene; Do. 1 -amino-2.5 din ethoxy4ch1oro-benzen Do. l-amino-3-mcthyl-4-methoxy-benzene. Do.LaminoJ-ethyl-Ehloro-bcnzene Violet. 2-amino-3methoxy-naphthaleueReddish violet. l-amino-il-(phenyl-amino-carbonyl)-benzene Do.l-amino-Ii-(dimethyl-amino-sulfonyl)-benzene Violet.1-amino-2-methy1-5-(ethyl-suHonyD-benzene Do. 2-ammo-anthraoenen; j.Reddlsh violet. 4-amiuo-acenaphthene Dark reddish violet.2-arnlno-carbazole Reddish violet. G-aminoJ-methyl-quinolin Dark violet.iAedlamino-ladimethylbenzene (half molecular Do.

proportlon). 1.tidia)mino-naphtha1ene (halt molecular propor- Do.

on I

v I'claim: V V 1. Asnewcompounds the azo dyestuffs of: the generalformula:

OCIH.

, CO-NH- 11 wherein R means a radical ofthe benzene, naphthalene,anthracene, acenaphthene, carbazole or quinoline series which radicalmay contain halogen, nitro-, alk0xy-, alkyl-, dialkylamino sulfonyl[(alkyl) N e 80,-],

or phenylaminocarbonyl- (G H NHCO) groups, and n means the nam her 1 or2 which compounds are insoluble in water and yield when produced onfibers reddish violet to blue dyeings of a good fastness. 2. As newcompounds the azo dyestuffs of the general formula:

' OO4H9 5 v 1 H1O N=N wherein R means a radical of the benzene serieswhich may contain halogen, nitro-, alkoxy-, alkyl-,dialkylamino-sulfonyl- [(alkyl) N-SO alkylsulfonylorphenylamino-carbonyl- (C H NHCO) groups,-which compounds are insolublein water and yield when produced on fibers reddish violet to bluedyeings of a good fastness.

3. As a new compound the azo dyestuif of the formula:

which compound is insoluble in water and yields when produced on fibersreddish violet dyeings of a good fastness.

4. As a new compound the azo dyestufi of the formula:

H0045 OH Cl O ONH which compound is insoluble in water and yields whenproduced on fibers blue dyeings of a good fastness.

5. Fiber dyed with the azo dyestufi's as claimed in claim 1. 6. Fiberdyed with the azo dyestuffs as claimed in claim 2. 7. Fiber dyed withthe azo dyestuif as claimed in claim 3.

8. Fiber dyed with the azo dyestuff as claimed in claim 4.

. In testimony whereof, I affix my signature.

ARTHUR ZITSOHER.

